Telluride is awesome, one of the best ski towns in Colorado and the best mountain in Colorado (imo), and by far the best region of Colorado. But I think your concerns are spot on, Telluride itself is far too expensive for most employees to live there, and more than anything else Telluride is small. It's one town in one small valley in one of the most remote parts of the continental US (nearest major city is ~8 hours away). Also my understanding is that due to the absurd cost of the town (I couldn't afford living there and I make >$200k) most service industry workers/resort employees commute from Montrose. But I'm not a local so I could be wrong. Either way, if you can score housing in Telluride you should absolutely do it.

After Telluride, I think CB and Steamboat are better than any of the other places you're considering. CB is a great town and a dope mountain, but suffers from some of the same housing market issues as Telluride (not as bad). Steamboat is a great mountain and the town is cool, but Steamboat itself doesn't have too much big terrain and it's hard to get to places with big terrain (Jackson is probably the best bet, though RMNP and the Gore range are there is the spring). Alternatively if you could make Ouray/Silverton work, those towns are cheaper than TRide (and Ouray is a pretty good place to be a bum).

Lastly, why are you restricting yourself to Colorado? There are some great places in Montana/Wyoming. But I would stay away from Tahoe/PNW/SLC/front range for crowding reasons personally.